ChemWiki - User contributions [en]

It:Vanillin

2006-11-23T10:48:23Z

Mjl105: /* Vanillin */ Addition of synthesis route

== Vanillin ==

Natural vanillin (or 4-hydroxy-3-methoxybenzaldehyde) is the main component of oil of vanilla, the essential oil (the fragrance of a plant) obtained from a type of orchid called ''Vanilla fragrans'' or vanilla orchid. Its formula is C<sub>8</sub>H<sub>8</sub>O<sub>3</sub> and its 3D structure is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Vanillin
WLViewer 3D 0

19 19 0 0 0 0 0 0 0 0999 V2000
11.4191 12.8675 -0.0044 O 0 0 0 0 0 0 0 0 0 1
10.1669 12.1722 -0.0027 C 0 0 0 0 0 0 0 0 0 2
12.6048 12.0611 -0.0025 C 0 0 0 0 0 0 0 0 0 3
13.7671 12.7164 -0.0020 C 0 0 0 0 0 0 0 0 0 4
12.6353 10.5423 0.0022 C 0 0 0 0 0 0 0 0 0 5
15.0368 11.9911 0.0005 C 0 0 0 0 0 0 0 0 0 6
11.4898 9.7471 0.0039 O 0 0 0 0 0 0 0 0 0 7
13.8093 9.9159 0.0043 C 0 0 0 0 0 0 0 0 0 8
16.2968 12.7160 -0.0001 C 0 0 0 0 0 0 0 0 0 9
15.0524 10.6634 0.0028 C 0 0 0 0 0 0 0 0 0 10
17.3581 12.0824 0.0007 O 0 0 0 0 0 0 0 0 0 11
9.4175 12.8342 -0.0043 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.6000 0.8150 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.5962 -0.8178 H 0 0 0 0 0 0 0 0 0 0
13.7700 13.7164 -0.0034 H 0 0 0 0 0 0 0 0 0 0
11.7531 8.7824 0.0070 H 0 0 0 0 0 0 0 0 0 0
13.8349 8.9162 0.0069 H 0 0 0 0 0 0 0 0 0 0
16.3049 13.7160 -0.0012 H 0 0 0 0 0 0 0 0 0 0
15.9257 10.1763 0.0035 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 2 0 0 0
2 12 1 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
4 15 1 0 0 0
7 16 1 0 0 0
8 17 1 0 0 0
9 18 1 0 0 0
10 19 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Most essential oils are obtained by distilling the leaves or petals of the plant over steam but oil of vanilla is extracted from the dried, fermented seed pods.

The majority of essentials oils are usually used in the perfume industry although some are also used in the food industry, particularly to flavour foods. Vanillin is used widely in both and because of this there is not enough natural supply to meet demand and so therefore has to be synthesised. This is mainly done by the oxidation of eugenol (or 2-methoxy-4-(2-propenyl)phenol) (which can be found in oil of bay found in bay leaves) which is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Eugenol
WLViewer 3D 0

24 24 0 0 0 0 0 0 0 0999 V2000
11.4061 12.8329 -0.0055 O 0 0 0 0 0 0 0 0 0 1
10.1915 12.0800 -0.0011 C 0 0 0 0 0 0 0 0 0 2
12.6254 12.0805 -0.0043 C 0 0 0 0 0 0 0 0 0 3
13.7605 12.7840 -0.0044 C 0 0 0 0 0 0 0 0 0 4
12.7188 10.5664 0.0012 C 0 0 0 0 0 0 0 0 0 5
15.0641 12.1130 0.0008 C 0 0 0 0 0 0 0 0 0 6
11.6086 9.7220 0.0027 O 0 0 0 0 0 0 0 0 0 7
13.9171 9.9898 0.0049 C 0 0 0 0 0 0 0 0 0 8
16.3338 12.9211 0.0030 C 0 0 0 0 0 0 0 0 0 9
15.1301 10.7861 0.0048 C 0 0 0 0 0 0 0 0 0 10
17.5243 11.9965 0.0008 C 0 0 0 0 0 0 0 0 0 11
18.7586 12.4953 -0.0000 C 0 0 0 0 0 0 0 0 0 12
9.4111 12.7052 -0.0025 H 0 0 0 0 0 0 0 0 0 0
10.1571 11.5066 0.8175 H 0 0 0 0 0 0 0 0 0 0
10.1550 11.5004 -0.8153 H 0 0 0 0 0 0 0 0 0 0
13.7207 13.7832 -0.0080 H 0 0 0 0 0 0 0 0 0 0
11.9136 8.7696 0.0065 H 0 0 0 0 0 0 0 0 0 0
13.9832 8.9920 0.0078 H 0 0 0 0 0 0 0 0 0 0
16.3609 13.4997 -0.8122 H 0 0 0 0 0 0 0 0 0 0
16.3607 13.4956 0.8211 H 0 0 0 0 0 0 0 0 0 0
16.0216 10.3331 0.0077 H 0 0 0 0 0 0 0 0 0 0
17.3866 11.0060 0.0000 H 0 0 0 0 0 0 0 0 0 0
19.5466 11.8798 -0.0015 H 0 0 0 0 0 0 0 0 0 0
18.8976 13.4856 0.0008 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 1 0 0 0
11 12 2 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
2 15 1 0 0 0
4 16 1 0 0 0
7 17 1 0 0 0
8 18 1 0 0 0
9 19 1 0 0 0
9 20 1 0 0 0
10 21 1 0 0 0
11 22 1 0 0 0
12 23 1 0 0 0
12 24 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

[[Image:Vanillin_synthesis_picture_MJL.gif|thumb|right|200|A reaction scheme showing how eugenol is oxidised to form vanillin]]

== Spectra ==

Click on a spectrum to view

[[Image:Vanillin_IR_Spectrum_MJL.PNG||thumb|left|200|IR spectrum of Vanillin]]
[[Image:Vanillin_UV Spectrum_MJL.PNG|thumb|left|200|UV spectrum of vanillin]]
[[Image:Vanillin_Mass_Spectrum_MJL.PNG|thumb|left|200|Mass spectrum of vanillin]]

File:Vanillin synthesis picture MJL.gif

2006-11-23T10:45:20Z

Mjl105: A reaction scheme showing how eugenol is oxidised to form vanillin.

A reaction scheme showing how eugenol is oxidised to form vanillin.

It:Adenosine Triphosphate

2006-11-23T10:40:19Z

Mjl105: Addition of 3D Jmol

== Adenosine Triphosphate ==

Adenosine Triphosphate (ATP) (C<sub>10</sub>H<sub>16</sub>O<sub>13</sub>N<sub>5</sub>P<sub>3</sub>) is found in muscles as an energy source.

<jmol>
<jmolApplet>
<size>500</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATP
WLViewer 3D 0

47 49 0 0 0 0 0 0 0 0999 V2000
16.1747 10.9080 1.0502 O 0 0 0 0 0 0 0 0 0 1
16.7822 11.4116 -0.1410 C 0 0 1 0 0 0 0 0 0 2
16.7113 12.9698 0.0421 C 0 0 2 0 0 0 0 0 0 3
18.3293 11.3438 -0.3596 C 0 0 2 0 0 0 0 0 0 4
15.4658 13.7093 -0.2516 N 0 0 0 0 0 0 0 0 0 5
17.8685 13.4980 -0.5005 O 0 0 0 0 0 0 0 0 0 6
18.9325 10.0708 -0.0836 O 0 0 0 0 0 0 0 0 0 7
18.8276 12.6051 0.2345 C 0 0 1 0 0 0 0 0 0 8
14.1141 13.3654 -0.0335 C 0 0 0 0 0 0 0 0 0 9
15.4356 15.1538 -0.4027 C 0 0 0 0 0 0 0 0 0 10
20.2497 13.0230 -0.1354 C 0 0 0 0 0 0 0 0 0 11
13.4069 14.4547 -0.1715 C 0 0 0 0 0 0 0 0 0 12
13.5235 12.1529 0.2765 N 0 0 0 0 0 0 0 0 0 13
14.2179 15.5540 -0.4153 N 0 0 0 0 0 0 0 0 0 14
21.2662 12.2003 0.3684 O 0 0 0 0 0 0 0 0 0 15
11.9938 14.4415 -0.0254 C 0 0 0 0 0 0 0 0 0 16
12.2450 12.1294 0.4069 C 0 0 0 0 0 0 0 0 0 17
22.5617 12.9741 0.1738 P 0 0 1 0 0 0 0 0 0 18
11.2273 15.6441 -0.1751 N 0 0 0 0 0 0 0 0 0 19
11.4431 13.3248 0.2475 N 0 0 0 0 0 0 0 0 0 20
23.7685 12.0688 -0.0441 O 0 0 0 0 0 0 0 0 0 21
22.4462 13.9489 -0.7426 O 0 0 0 0 0 0 0 0 0 22
22.8783 13.7620 1.4187 O 0 0 0 0 0 0 0 0 0 23
25.1314 12.8088 -0.0644 P 0 0 1 0 0 0 0 0 0 24
25.0619 14.3488 -0.0444 O 0 0 0 0 0 0 0 0 0 25
25.8441 12.3892 0.9932 O 0 0 0 0 0 0 0 0 0 26
26.0476 12.2764 -1.1401 O 0 0 0 0 0 0 0 0 0 27
26.4367 15.0409 -0.1381 P 0 0 0 0 0 0 0 0 0 28
27.1540 14.5246 -1.1463 O 0 0 0 0 0 0 0 0 0 29
26.2857 16.5363 -0.2585 O 0 0 0 0 0 0 0 0 0 30
27.2314 14.6905 1.0941 O 0 0 0 0 0 0 0 0 0 31
16.1726 9.9083 1.0270 H 0 0 0 0 0 0 0 0 0 0
16.3239 10.8849 -0.8569 H 0 0 0 0 0 0 0 0 0 0
16.6567 13.1231 1.0287 H 0 0 0 0 0 0 0 0 0 0
18.6315 11.3329 -1.3128 H 0 0 0 0 0 0 0 0 0 0
19.9169 10.1246 -0.2507 H 0 0 0 0 0 0 0 0 0 0
18.8664 12.5909 1.2336 H 0 0 0 0 0 0 0 0 0 0
16.2391 15.7436 -0.4840 H 0 0 0 0 0 0 0 0 0 0
20.3209 13.0263 -1.1329 H 0 0 0 0 0 0 0 0 0 0
20.4001 13.9482 0.2130 H 0 0 0 0 0 0 0 0 0 0
11.7929 11.2642 0.6237 H 0 0 0 0 0 0 0 0 0 0
10.2332 15.6199 -0.0695 H 0 0 0 0 0 0 0 0 0 0
11.6869 16.5070 -0.3852 H 0 0 0 0 0 0 0 0 0 0
23.7301 14.2685 1.2856 H 0 0 0 0 0 0 0 0 0 0
26.9126 12.7778 -1.1201 H 0 0 0 0 0 0 0 0 0 0
27.1898 16.9594 -0.3175 H 0 0 0 0 0 0 0 0 0 0
28.1277 15.1318 1.0499 H 0 0 0 0 0 0 0 0 0 0
2 1 1 1 0 0
2 3 1 0 0 0
2 4 1 0 0 0
3 5 1 6 0 0
3 6 1 0 0 0
4 7 1 1 0 0
4 8 1 0 0 0
5 9 1 0 0 0
5 10 1 0 0 0
6 8 1 0 0 0
8 11 1 6 0 0
9 12 2 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
12 14 1 0 0 0
12 16 1 0 0 0
13 17 2 0 0 0
15 18 1 0 0 0
16 19 1 0 0 0
16 20 2 0 0 0
17 20 1 0 0 0
18 21 1 0 0 0
18 22 2 0 0 0
18 23 1 0 0 0
21 24 1 0 0 0
24 25 1 0 0 0
24 26 2 0 0 0
24 27 1 0 0 0
25 28 1 0 0 0
28 29 2 0 0 0
28 30 1 0 0 0
28 31 1 0 0 0
1 32 1 0 0 0
2 33 1 0 0 0
3 34 1 0 0 0
4 35 1 0 0 0
7 36 1 0 0 0
8 37 1 0 0 0
10 38 1 0 0 0
11 39 1 0 0 0
11 40 1 0 0 0
17 41 1 0 0 0
19 42 1 0 0 0
19 43 1 0 0 0
23 44 1 0 0 0
27 45 1 0 0 0
30 46 1 0 0 0
31 47 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

It:projects

2006-11-23T10:36:45Z

Mjl105: /* Supplemental Project Page */ Addition of ATP page

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| bgcolor="#CCFF00" |01
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|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
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| bgcolor="#CCFF00" |22
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|-
|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
|-
| bgcolor="#CCFF00" |24
| bgcolor="#66FF99" | [[it:Sertraline|Sertraline HCl (anti-depression)]]
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| bgcolor="#CCFF00" |25
| bgcolor="#CCFF00" | [[it:Ceftriaxone|Ceftriaxone (Gonorrhoea)]]
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| bgcolor="#CCFF00" |26
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| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
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*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
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*[[it:Melatonin|Melatonin: The All-Natural Nightcap]]
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It:Pelargonidin

2006-11-23T10:30:47Z

Mjl105: /* What is Pelargonidin? */ Adjustment to picture

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|right|200|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|General anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:28:27Z

Mjl105: /* Cyanidin */

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|right|200|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:27:26Z

Mjl105: /* Cyanidin */

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:27:05Z

Mjl105: /* Cyanidin */

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|right|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:26:47Z

Mjl105: /* Cyanidin */

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|right|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

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==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:24:36Z

Mjl105: /* Cyanidin */ Format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
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<inlineContents>Pelargonidin
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31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
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<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|right|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

----

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:23:56Z

Mjl105: /* Cyanidin */ Picture format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
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<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
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<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|right|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:23:07Z

Mjl105: /* Structures of Pelargonidin */ Sugar bonding

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

When anthocyanidins bond to sugars they become anthocyanins (a type of glycoside). This is achived by removing a proton from an OH group and bonding to a sugar molecule (such as glucose).

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:17:17Z

Mjl105: /* Structures of Pelargonidin */

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:16:42Z

Mjl105: /* Cyanidin */

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|left|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:15:16Z

Mjl105: /* Cyanidin */ Picture format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|left|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:14:29Z

Mjl105: /* Structures of Pelargonidin */ Picture format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|left|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:12:12Z

Mjl105: /* Structures of Pelargonidin */ Picture format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
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<inlineContents>Pelargonidin
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31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

'''Colours of Pelargonidin'''

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|left|200|Colour due to pelargonidin]][[Image:Red_Geranium_MJL.jpg|thumb|left|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
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<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:11:32Z

Mjl105: /* Cyanidin */ Picture format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
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<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

Colours of Pelargonidin

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
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<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blackcurrant_MJL.jpg|thumb|left|200|Ripe blackberries]][[Image:Blue_Cornflower_MJL.JPG|thumb|left|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]][[Image:Red_Poppy_MJL.jpg|thumb|left|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:08:16Z

Mjl105: /* Cyanidin */ Acidity pictures

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

Colours of Pelargonidin

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

[[Image:Blackcurrant_MJL.jpg|thumb|right|200|Ripe blackberries]]

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

[[Image:Blue_Cornflower_MJL.JPG|thumb|right|200|The colour of the blue cornflower (''Centaurea cyanus'') is caused by cyanidin in basic conditions]]
[[Image:Red_Poppy_MJL.jpg|thumb|right|200|Differing by the addition of a single H atom, the colour of the red poppy (''Papaver rhoeas'') is caused by the cyanidin in acidic conditions]]

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:02:40Z

Mjl105: /* Cyanidin */ Cyanidin pictures

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

Colours of Pelargonidin

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which contributes to the colour of ripe blackcurrants.

[[Image:Blackcurrant_MJL.jpg|thumb|right|200|Ripe blackberries]]

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T10:00:07Z

Mjl105: /* Cyanidin */ Colour of Cyanidin

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

Colours of Pelargonidin

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Cyanidin produces a magenta colour, which makes up the colour of ripe backberries.

An example of how their colour is changed by acidity is shown by cyanidin. Cyanidin is responsible for both the colour of the blue cornflower (in basic conditions) and the red poppy (in acidic conditions).

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:56:23Z

Mjl105: /* Colours of Pelargonidin */ Adjustment to title format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

Colours of Pelargonidin

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:55:24Z

Mjl105: /* Colours of Pelargonidin */ Adjustment to text

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Colours of Pelargonidin ==

Pelargonidin itself produces an orange red colour, seen in red geraniums, and ripe raspberries and strawberries to name but a few.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:53:21Z

Mjl105: /* Colours of Pelargonidin */ Page layout

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Colours of Pelargonidin ==

Pelargonidin is responsible for many red colours, one of which the red geranium.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|right|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|right|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:52:23Z

Mjl105: /* Cyanidin */ Adjustment on page

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Colours of Pelargonidin ==

Pelargonidin is responsible for many red colours, one of which the red geranium.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|left|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|left|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:51:42Z

Mjl105: /* Colours of Pelargonidin */ First information about colour

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Colours of Pelargonidin ==

Pelargonidin is responsible for many red colours, one of which the red geranium.

[[Image:Pelargonidin_Colour_MJL.jpg|thumb|left|200|Colour due to pelargonidin]]
[[Image:Red_Geranium_MJL.jpg|thumb|left|200|Red geranium (genus ''Pelargonium'')]]

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:46:15Z

Mjl105: /* '''Flavonoids, Nature's Paintbox''' */ Addition of Autumn picture

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]][[Image:Autumn_picture_MJL.jpg|Autumn picture of treetops]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Colours of Pelargonidin ==

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:42:16Z

Mjl105: /* Structures of Pelargonidin */ Title

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Colours of Pelargonidin ==

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:41:21Z

Mjl105: /* '''Flavonoids, Nature's Paintbox''' */ Slightly adjustment of text

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways, by attaching different groups (mainly OH or OMe) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:Pelargonidin

2006-11-23T09:40:36Z

Mjl105: /* Structures of Pelargonidin */ Format of headings

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways. By attaching different groups (mainly OH) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

== Cyanidin ==

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

File:Red Poppy MJL.jpg

2006-11-23T09:38:12Z

Mjl105: Red Poppy (''Papaver rhoeas'')

Red Poppy (''Papaver rhoeas'')

File:Red Geranium MJL.jpg

2006-11-23T09:37:15Z

Mjl105: Red Gernanium (genus ''Pelargonium'')

Red Gernanium (genus ''Pelargonium'')

File:Peony MJL.jpg

2006-11-23T09:36:16Z

Mjl105: Peony (genus ''Camelia'')

Peony (genus ''Camelia'')

File:Pelargonidin Colour MJL.jpg

2006-11-23T09:35:23Z

Mjl105: Colour of flower produced by pelargonidin

Colour of flower produced by pelargonidin

File:Blue Cornflower MJL.JPG

2006-11-23T09:33:56Z

Mjl105: Blue Cornflower (''Centaurea cyanus'')

Blue Cornflower (''Centaurea cyanus'')

File:Blackcurrant MJL.jpg

2006-11-23T09:31:52Z

Mjl105: Blackcurrants

Blackcurrants

File:Autumn picture MJL.jpg

2006-11-23T09:30:55Z

Mjl105: Autumn picture

Autumn picture

It:Vanillin

2006-11-17T11:42:05Z

Mjl105: /* Spectra */ Addition of UV spectrum

== Vanillin ==

Natural vanillin (or 4-hydroxy-3-methoxybenzaldehyde) is the main component of oil of vanilla, the essential oil (the fragrance of a plant) obtained from a type of orchid called ''Vanilla fragrans'' or vanilla orchid. Its formula is C<sub>8</sub>H<sub>8</sub>O<sub>3</sub> and its 3D structure is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Vanillin
WLViewer 3D 0

19 19 0 0 0 0 0 0 0 0999 V2000
11.4191 12.8675 -0.0044 O 0 0 0 0 0 0 0 0 0 1
10.1669 12.1722 -0.0027 C 0 0 0 0 0 0 0 0 0 2
12.6048 12.0611 -0.0025 C 0 0 0 0 0 0 0 0 0 3
13.7671 12.7164 -0.0020 C 0 0 0 0 0 0 0 0 0 4
12.6353 10.5423 0.0022 C 0 0 0 0 0 0 0 0 0 5
15.0368 11.9911 0.0005 C 0 0 0 0 0 0 0 0 0 6
11.4898 9.7471 0.0039 O 0 0 0 0 0 0 0 0 0 7
13.8093 9.9159 0.0043 C 0 0 0 0 0 0 0 0 0 8
16.2968 12.7160 -0.0001 C 0 0 0 0 0 0 0 0 0 9
15.0524 10.6634 0.0028 C 0 0 0 0 0 0 0 0 0 10
17.3581 12.0824 0.0007 O 0 0 0 0 0 0 0 0 0 11
9.4175 12.8342 -0.0043 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.6000 0.8150 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.5962 -0.8178 H 0 0 0 0 0 0 0 0 0 0
13.7700 13.7164 -0.0034 H 0 0 0 0 0 0 0 0 0 0
11.7531 8.7824 0.0070 H 0 0 0 0 0 0 0 0 0 0
13.8349 8.9162 0.0069 H 0 0 0 0 0 0 0 0 0 0
16.3049 13.7160 -0.0012 H 0 0 0 0 0 0 0 0 0 0
15.9257 10.1763 0.0035 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 2 0 0 0
2 12 1 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
4 15 1 0 0 0
7 16 1 0 0 0
8 17 1 0 0 0
9 18 1 0 0 0
10 19 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Most essential oils are obtained by distilling the leaves or petals of the plant over steam but oil of vanilla is extracted from the dried, fermented seed pods.

The majority of essentials oils are usually used in the perfume industry although some are also used in the food industry, particularly to flavour foods. Vanillin is used widely in both and because of this there is not enough natural supply to meet demand and so therefore has to be synthesised. This is mainly done by the oxidation of eugenol (or 2-methoxy-4-(2-propenyl)phenol) (which can be found in oil of bay found in bay leaves) which is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Eugenol
WLViewer 3D 0

24 24 0 0 0 0 0 0 0 0999 V2000
11.4061 12.8329 -0.0055 O 0 0 0 0 0 0 0 0 0 1
10.1915 12.0800 -0.0011 C 0 0 0 0 0 0 0 0 0 2
12.6254 12.0805 -0.0043 C 0 0 0 0 0 0 0 0 0 3
13.7605 12.7840 -0.0044 C 0 0 0 0 0 0 0 0 0 4
12.7188 10.5664 0.0012 C 0 0 0 0 0 0 0 0 0 5
15.0641 12.1130 0.0008 C 0 0 0 0 0 0 0 0 0 6
11.6086 9.7220 0.0027 O 0 0 0 0 0 0 0 0 0 7
13.9171 9.9898 0.0049 C 0 0 0 0 0 0 0 0 0 8
16.3338 12.9211 0.0030 C 0 0 0 0 0 0 0 0 0 9
15.1301 10.7861 0.0048 C 0 0 0 0 0 0 0 0 0 10
17.5243 11.9965 0.0008 C 0 0 0 0 0 0 0 0 0 11
18.7586 12.4953 -0.0000 C 0 0 0 0 0 0 0 0 0 12
9.4111 12.7052 -0.0025 H 0 0 0 0 0 0 0 0 0 0
10.1571 11.5066 0.8175 H 0 0 0 0 0 0 0 0 0 0
10.1550 11.5004 -0.8153 H 0 0 0 0 0 0 0 0 0 0
13.7207 13.7832 -0.0080 H 0 0 0 0 0 0 0 0 0 0
11.9136 8.7696 0.0065 H 0 0 0 0 0 0 0 0 0 0
13.9832 8.9920 0.0078 H 0 0 0 0 0 0 0 0 0 0
16.3609 13.4997 -0.8122 H 0 0 0 0 0 0 0 0 0 0
16.3607 13.4956 0.8211 H 0 0 0 0 0 0 0 0 0 0
16.0216 10.3331 0.0077 H 0 0 0 0 0 0 0 0 0 0
17.3866 11.0060 0.0000 H 0 0 0 0 0 0 0 0 0 0
19.5466 11.8798 -0.0015 H 0 0 0 0 0 0 0 0 0 0
18.8976 13.4856 0.0008 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 1 0 0 0
11 12 2 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
2 15 1 0 0 0
4 16 1 0 0 0
7 17 1 0 0 0
8 18 1 0 0 0
9 19 1 0 0 0
9 20 1 0 0 0
10 21 1 0 0 0
11 22 1 0 0 0
12 23 1 0 0 0
12 24 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

== Spectra ==

Click on a spectrum to view

[[Image:Vanillin_IR_Spectrum_MJL.PNG||thumb|left|200|IR spectrum of Vanillin]]
[[Image:Vanillin_UV Spectrum_MJL.PNG|thumb|left|200|UV spectrum of vanillin]]
[[Image:Vanillin_Mass_Spectrum_MJL.PNG|thumb|left|200|Mass spectrum of vanillin]]

File:Vanillin UV Spectrum MJL.PNG

2006-11-17T11:38:37Z

Mjl105: UV spectrum of vanillin from NIST

UV spectrum of vanillin from NIST

It:Vanillin

2006-11-17T11:34:17Z

Mjl105: /* Spectra */ Addition of mass spectrum

== Vanillin ==

Natural vanillin (or 4-hydroxy-3-methoxybenzaldehyde) is the main component of oil of vanilla, the essential oil (the fragrance of a plant) obtained from a type of orchid called ''Vanilla fragrans'' or vanilla orchid. Its formula is C<sub>8</sub>H<sub>8</sub>O<sub>3</sub> and its 3D structure is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Vanillin
WLViewer 3D 0

19 19 0 0 0 0 0 0 0 0999 V2000
11.4191 12.8675 -0.0044 O 0 0 0 0 0 0 0 0 0 1
10.1669 12.1722 -0.0027 C 0 0 0 0 0 0 0 0 0 2
12.6048 12.0611 -0.0025 C 0 0 0 0 0 0 0 0 0 3
13.7671 12.7164 -0.0020 C 0 0 0 0 0 0 0 0 0 4
12.6353 10.5423 0.0022 C 0 0 0 0 0 0 0 0 0 5
15.0368 11.9911 0.0005 C 0 0 0 0 0 0 0 0 0 6
11.4898 9.7471 0.0039 O 0 0 0 0 0 0 0 0 0 7
13.8093 9.9159 0.0043 C 0 0 0 0 0 0 0 0 0 8
16.2968 12.7160 -0.0001 C 0 0 0 0 0 0 0 0 0 9
15.0524 10.6634 0.0028 C 0 0 0 0 0 0 0 0 0 10
17.3581 12.0824 0.0007 O 0 0 0 0 0 0 0 0 0 11
9.4175 12.8342 -0.0043 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.6000 0.8150 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.5962 -0.8178 H 0 0 0 0 0 0 0 0 0 0
13.7700 13.7164 -0.0034 H 0 0 0 0 0 0 0 0 0 0
11.7531 8.7824 0.0070 H 0 0 0 0 0 0 0 0 0 0
13.8349 8.9162 0.0069 H 0 0 0 0 0 0 0 0 0 0
16.3049 13.7160 -0.0012 H 0 0 0 0 0 0 0 0 0 0
15.9257 10.1763 0.0035 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 2 0 0 0
2 12 1 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
4 15 1 0 0 0
7 16 1 0 0 0
8 17 1 0 0 0
9 18 1 0 0 0
10 19 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Most essential oils are obtained by distilling the leaves or petals of the plant over steam but oil of vanilla is extracted from the dried, fermented seed pods.

The majority of essentials oils are usually used in the perfume industry although some are also used in the food industry, particularly to flavour foods. Vanillin is used widely in both and because of this there is not enough natural supply to meet demand and so therefore has to be synthesised. This is mainly done by the oxidation of eugenol (or 2-methoxy-4-(2-propenyl)phenol) (which can be found in oil of bay found in bay leaves) which is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Eugenol
WLViewer 3D 0

24 24 0 0 0 0 0 0 0 0999 V2000
11.4061 12.8329 -0.0055 O 0 0 0 0 0 0 0 0 0 1
10.1915 12.0800 -0.0011 C 0 0 0 0 0 0 0 0 0 2
12.6254 12.0805 -0.0043 C 0 0 0 0 0 0 0 0 0 3
13.7605 12.7840 -0.0044 C 0 0 0 0 0 0 0 0 0 4
12.7188 10.5664 0.0012 C 0 0 0 0 0 0 0 0 0 5
15.0641 12.1130 0.0008 C 0 0 0 0 0 0 0 0 0 6
11.6086 9.7220 0.0027 O 0 0 0 0 0 0 0 0 0 7
13.9171 9.9898 0.0049 C 0 0 0 0 0 0 0 0 0 8
16.3338 12.9211 0.0030 C 0 0 0 0 0 0 0 0 0 9
15.1301 10.7861 0.0048 C 0 0 0 0 0 0 0 0 0 10
17.5243 11.9965 0.0008 C 0 0 0 0 0 0 0 0 0 11
18.7586 12.4953 -0.0000 C 0 0 0 0 0 0 0 0 0 12
9.4111 12.7052 -0.0025 H 0 0 0 0 0 0 0 0 0 0
10.1571 11.5066 0.8175 H 0 0 0 0 0 0 0 0 0 0
10.1550 11.5004 -0.8153 H 0 0 0 0 0 0 0 0 0 0
13.7207 13.7832 -0.0080 H 0 0 0 0 0 0 0 0 0 0
11.9136 8.7696 0.0065 H 0 0 0 0 0 0 0 0 0 0
13.9832 8.9920 0.0078 H 0 0 0 0 0 0 0 0 0 0
16.3609 13.4997 -0.8122 H 0 0 0 0 0 0 0 0 0 0
16.3607 13.4956 0.8211 H 0 0 0 0 0 0 0 0 0 0
16.0216 10.3331 0.0077 H 0 0 0 0 0 0 0 0 0 0
17.3866 11.0060 0.0000 H 0 0 0 0 0 0 0 0 0 0
19.5466 11.8798 -0.0015 H 0 0 0 0 0 0 0 0 0 0
18.8976 13.4856 0.0008 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 1 0 0 0
11 12 2 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
2 15 1 0 0 0
4 16 1 0 0 0
7 17 1 0 0 0
8 18 1 0 0 0
9 19 1 0 0 0
9 20 1 0 0 0
10 21 1 0 0 0
11 22 1 0 0 0
12 23 1 0 0 0
12 24 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

== Spectra ==

Click on a spectrum to view

[[Image:Vanillin_IR_Spectrum_MJL.PNG||thumb|left|200|IR spectrum of Vanillin]][[Image:Vanillin_Mass_Spectrum_MJL.PNG|thumb|right|200|Mass spectrum of vanillin]]

File:Vanillin Mass Spectrum MJL.PNG

2006-11-17T11:19:59Z

Mjl105: Mass spectrum of vanillin from NIST

Mass spectrum of vanillin from NIST

It:Vanillin

2006-11-16T11:39:51Z

Mjl105: /* Vanillin */ Addition of IR spectrum

== Vanillin ==

Natural vanillin (or 4-hydroxy-3-methoxybenzaldehyde) is the main component of oil of vanilla, the essential oil (the fragrance of a plant) obtained from a type of orchid called ''Vanilla fragrans'' or vanilla orchid. Its formula is C<sub>8</sub>H<sub>8</sub>O<sub>3</sub> and its 3D structure is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Vanillin
WLViewer 3D 0

19 19 0 0 0 0 0 0 0 0999 V2000
11.4191 12.8675 -0.0044 O 0 0 0 0 0 0 0 0 0 1
10.1669 12.1722 -0.0027 C 0 0 0 0 0 0 0 0 0 2
12.6048 12.0611 -0.0025 C 0 0 0 0 0 0 0 0 0 3
13.7671 12.7164 -0.0020 C 0 0 0 0 0 0 0 0 0 4
12.6353 10.5423 0.0022 C 0 0 0 0 0 0 0 0 0 5
15.0368 11.9911 0.0005 C 0 0 0 0 0 0 0 0 0 6
11.4898 9.7471 0.0039 O 0 0 0 0 0 0 0 0 0 7
13.8093 9.9159 0.0043 C 0 0 0 0 0 0 0 0 0 8
16.2968 12.7160 -0.0001 C 0 0 0 0 0 0 0 0 0 9
15.0524 10.6634 0.0028 C 0 0 0 0 0 0 0 0 0 10
17.3581 12.0824 0.0007 O 0 0 0 0 0 0 0 0 0 11
9.4175 12.8342 -0.0043 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.6000 0.8150 H 0 0 0 0 0 0 0 0 0 0
10.1039 11.5962 -0.8178 H 0 0 0 0 0 0 0 0 0 0
13.7700 13.7164 -0.0034 H 0 0 0 0 0 0 0 0 0 0
11.7531 8.7824 0.0070 H 0 0 0 0 0 0 0 0 0 0
13.8349 8.9162 0.0069 H 0 0 0 0 0 0 0 0 0 0
16.3049 13.7160 -0.0012 H 0 0 0 0 0 0 0 0 0 0
15.9257 10.1763 0.0035 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 2 0 0 0
2 12 1 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
4 15 1 0 0 0
7 16 1 0 0 0
8 17 1 0 0 0
9 18 1 0 0 0
10 19 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

Most essential oils are obtained by distilling the leaves or petals of the plant over steam but oil of vanilla is extracted from the dried, fermented seed pods.

The majority of essentials oils are usually used in the perfume industry although some are also used in the food industry, particularly to flavour foods. Vanillin is used widely in both and because of this there is not enough natural supply to meet demand and so therefore has to be synthesised. This is mainly done by the oxidation of eugenol (or 2-methoxy-4-(2-propenyl)phenol) (which can be found in oil of bay found in bay leaves) which is shown below:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Eugenol
WLViewer 3D 0

24 24 0 0 0 0 0 0 0 0999 V2000
11.4061 12.8329 -0.0055 O 0 0 0 0 0 0 0 0 0 1
10.1915 12.0800 -0.0011 C 0 0 0 0 0 0 0 0 0 2
12.6254 12.0805 -0.0043 C 0 0 0 0 0 0 0 0 0 3
13.7605 12.7840 -0.0044 C 0 0 0 0 0 0 0 0 0 4
12.7188 10.5664 0.0012 C 0 0 0 0 0 0 0 0 0 5
15.0641 12.1130 0.0008 C 0 0 0 0 0 0 0 0 0 6
11.6086 9.7220 0.0027 O 0 0 0 0 0 0 0 0 0 7
13.9171 9.9898 0.0049 C 0 0 0 0 0 0 0 0 0 8
16.3338 12.9211 0.0030 C 0 0 0 0 0 0 0 0 0 9
15.1301 10.7861 0.0048 C 0 0 0 0 0 0 0 0 0 10
17.5243 11.9965 0.0008 C 0 0 0 0 0 0 0 0 0 11
18.7586 12.4953 -0.0000 C 0 0 0 0 0 0 0 0 0 12
9.4111 12.7052 -0.0025 H 0 0 0 0 0 0 0 0 0 0
10.1571 11.5066 0.8175 H 0 0 0 0 0 0 0 0 0 0
10.1550 11.5004 -0.8153 H 0 0 0 0 0 0 0 0 0 0
13.7207 13.7832 -0.0080 H 0 0 0 0 0 0 0 0 0 0
11.9136 8.7696 0.0065 H 0 0 0 0 0 0 0 0 0 0
13.9832 8.9920 0.0078 H 0 0 0 0 0 0 0 0 0 0
16.3609 13.4997 -0.8122 H 0 0 0 0 0 0 0 0 0 0
16.3607 13.4956 0.8211 H 0 0 0 0 0 0 0 0 0 0
16.0216 10.3331 0.0077 H 0 0 0 0 0 0 0 0 0 0
17.3866 11.0060 0.0000 H 0 0 0 0 0 0 0 0 0 0
19.5466 11.8798 -0.0015 H 0 0 0 0 0 0 0 0 0 0
18.8976 13.4856 0.0008 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
1 3 1 0 0 0
3 4 2 0 0 0
3 5 1 0 0 0
4 6 1 0 0 0
5 7 1 0 0 0
5 8 2 0 0 0
6 9 1 0 0 0
6 10 2 0 0 0
8 10 1 0 0 0
9 11 1 0 0 0
11 12 2 0 0 0
2 13 1 0 0 0
2 14 1 0 0 0
2 15 1 0 0 0
4 16 1 0 0 0
7 17 1 0 0 0
8 18 1 0 0 0
9 19 1 0 0 0
9 20 1 0 0 0
10 21 1 0 0 0
11 22 1 0 0 0
12 23 1 0 0 0
12 24 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

== Spectra ==

Click on a spectrum to view

[[Image:Vanillin_IR_Spectrum_MJL.PNG||thumb|left|1000|IR spectrum of Vanillin]]

File:Vanillin IR Spectrum MJL.PNG

2006-11-16T11:34:32Z

Mjl105: IR spectrum of vanillin from NIST

IR spectrum of vanillin from NIST

It:Pelargonidin

2006-11-16T11:09:40Z

Mjl105: /* '''Flavonoids, Nature's Paintbox''' */ Adjustment of picture format

== '''Flavonoids, Nature's Paintbox''' ==

Flavonids are responsible for many bright colours in nature.

[[Image:Flavonid_MJL.gif|Flavonid 2D structure]]

In this basic structure only the two end rings are aromatic.

Various different colours can be formed by varying the basic flavonid structure in three main ways. By attaching different groups (mainly OH) to different points around the rings; by bonding to different sugars (to form glycosides); or by adjusting the acidity of their surroundings.

==Structures of Pelargonidin==

Pelargonidin is a simple anthocyanidin (a class of flavonid) with the following structure:

[[Image:Pelargonidin_MJL.gif|thumb|Pelargonidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Pelargonidin
WLViewer 3D 0

31 33 0 0 0 0 0 0 0 0999 V2000
12.7970 11.6294 -0.0062 O 0 0 0 0 0 0 0 0 0 1
12.8081 13.0150 -0.0035 C 0 0 0 0 0 0 0 0 0 2
14.0814 13.7220 -0.0005 C 0 0 0 0 0 0 0 0 0 3
11.6669 13.6981 -0.0023 C 0 0 0 0 0 0 0 0 0 4
14.1264 15.0524 0.0007 C 0 0 0 0 0 0 0 0 0 5
15.2970 12.9728 0.0000 C 0 0 0 0 0 0 0 0 0 6
11.7024 15.1646 0.0013 C 0 0 0 0 0 0 0 0 0 7
15.3425 15.7179 -0.0003 O 0 3 0 0 0 0 0 0 0 8
12.8708 15.8096 0.0023 C 0 0 0 0 0 0 0 0 0 9
16.4460 13.6215 -0.0000 C 0 0 0 0 0 0 0 0 0 10
10.5177 15.8822 0.0031 O 0 0 0 0 0 0 0 0 0 11
16.4345 15.1110 -0.0011 C 0 0 0 0 0 0 0 0 0 12
17.6205 12.8810 0.0001 O 0 0 0 0 0 0 0 0 0 13
17.7180 15.8874 0.0001 C 0 0 0 0 0 0 0 0 0 14
17.7048 17.2205 -0.0046 C 0 0 0 0 0 0 0 0 0 15
19.0118 15.1908 0.0061 C 0 0 0 0 0 0 0 0 0 16
18.9809 17.9651 -0.0043 C 0 0 0 0 0 0 0 0 0 17
20.1571 15.8606 0.0066 C 0 0 0 0 0 0 0 0 0 18
20.1435 17.3097 0.0015 C 0 0 0 0 0 0 0 0 0 19
21.3451 18.0059 0.0037 O 0 0 0 0 0 0 0 0 0 20
11.8518 11.3031 -0.0080 H 0 0 0 0 0 0 0 0 0 0
10.7910 13.2155 -0.0039 H 0 0 0 0 0 0 0 0 0 0
15.2778 11.9730 0.0004 H 0 0 0 0 0 0 0 0 0 0
12.8899 16.8094 0.0041 H 0 0 0 0 0 0 0 0 0 0
10.7206 16.8614 0.0055 H 0 0 0 0 0 0 0 0 0 0
18.4056 13.5003 0.0000 H 0 0 0 0 0 0 0 0 0 0
16.8352 17.7142 -0.0083 H 0 0 0 0 0 0 0 0 0 0
19.0295 14.1910 0.0098 H 0 0 0 0 0 0 0 0 0 0
18.9735 18.9651 -0.0085 H 0 0 0 0 0 0 0 0 0 0
21.0268 15.3671 0.0106 H 0 0 0 0 0 0 0 0 0 0
22.1065 17.3577 0.0081 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
5 9 1 0 0 0
6 10 2 0 0 0
7 9 2 0 0 0
7 11 1 0 0 0
8 12 2 0 0 0
10 12 1 0 0 0
10 13 1 0 0 0
12 14 1 0 0 0
14 15 2 0 0 0
14 16 1 0 0 0
15 17 1 0 0 0
16 18 2 0 0 0
17 19 2 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
1 21 1 0 0 0
4 22 1 0 0 0
6 23 1 0 0 0
9 24 1 0 0 0
11 25 1 0 0 0
13 26 1 0 0 0
15 27 1 0 0 0
16 28 1 0 0 0
17 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

All three rings here are aromatic and the ‘central’ oxygen has a formal charge of +1 (and thus this molecule is sometimes shown with a counter anion such as Cl<sup>-</sup>).

Cyanidin is also an anthocyanidin and differs from pelargonidin by the addition of an OH to the meta position on the right hand ring and its structure is shown below:

[[Image:Cyanidin_MJL.gif|thumb|Cyanidin 2D structure]]

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Cyanidin
WLViewer 3D 0

32 34 0 0 0 0 0 0 0 0999 V2000
17.6462 12.9341 -0.0048 O 0 0 0 0 0 0 0 0 0 1
16.4712 13.6724 -0.0037 C 0 0 0 0 0 0 0 0 0 2
16.4573 15.1648 -0.0041 C 0 0 0 0 0 0 0 0 0 3
15.3249 13.0194 -0.0026 C 0 0 0 0 0 0 0 0 0 4
15.3617 15.7682 -0.0043 O 0 3 0 0 0 0 0 0 0 5
17.7481 15.9415 -0.0008 C 0 0 0 0 0 0 0 0 0 6
14.1090 13.7632 -0.0012 C 0 0 0 0 0 0 0 0 0 7
14.1463 15.0937 -0.0028 C 0 0 0 0 0 0 0 0 0 8
17.7468 17.2747 -0.0026 C 0 0 0 0 0 0 0 0 0 9
19.0378 15.2374 0.0036 C 0 0 0 0 0 0 0 0 0 10
12.8456 13.0514 0.0031 C 0 0 0 0 0 0 0 0 0 11
12.8832 15.8411 -0.0027 C 0 0 0 0 0 0 0 0 0 12
19.0340 18.0081 -0.0009 C 0 0 0 0 0 0 0 0 0 13
20.1893 15.8964 0.0046 C 0 0 0 0 0 0 0 0 0 14
12.8461 11.6662 0.0050 O 0 0 0 0 0 0 0 0 0 15
11.6989 13.7247 0.0062 C 0 0 0 0 0 0 0 0 0 16
11.7207 15.1880 0.0026 C 0 0 0 0 0 0 0 0 0 17
19.0389 19.3912 -0.0027 O 0 0 0 0 0 0 0 0 0 18
20.1898 17.3428 0.0025 C 0 0 0 0 0 0 0 0 0 19
10.5307 15.8963 0.0041 O 0 0 0 0 0 0 0 0 0 20
21.3969 18.0288 0.0047 O 0 0 0 0 0 0 0 0 0 21
17.4273 11.9584 -0.0043 H 0 0 0 0 0 0 0 0 0 0
15.3094 12.0196 -0.0027 H 0 0 0 0 0 0 0 0 0 0
16.8820 17.7767 -0.0051 H 0 0 0 0 0 0 0 0 0 0
19.0479 14.2375 0.0060 H 0 0 0 0 0 0 0 0 0 0
12.8944 16.8410 -0.0066 H 0 0 0 0 0 0 0 0 0 0
21.0542 15.3946 0.0068 H 0 0 0 0 0 0 0 0 0 0
11.9036 11.3321 0.0080 H 0 0 0 0 0 0 0 0 0 0
10.8274 13.2344 0.0110 H 0 0 0 0 0 0 0 0 0 0
19.9827 19.7216 -0.0012 H 0 0 0 0 0 0 0 0 0 0
9.7618 15.2570 0.0082 H 0 0 0 0 0 0 0 0 0 0
22.1528 17.3742 0.0071 H 0 0 0 0 0 0 0 0 0 0
1 2 1 0 0 0
2 3 1 0 0 0
2 4 2 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
7 8 2 0 0 0
7 11 1 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
11 16 2 0 0 0
12 17 2 0 0 0
13 18 1 0 0 0
13 19 2 0 0 0
14 19 1 0 0 0
16 17 1 0 0 0
17 20 1 0 0 0
19 21 1 0 0 0
1 22 1 0 0 0
4 23 1 0 0 0
9 24 1 0 0 0
10 25 1 0 0 0
12 26 1 0 0 0
14 27 1 0 0 0
15 28 1 0 0 0
16 29 1 0 0 0
18 30 1 0 0 0
20 31 1 0 0 0
21 32 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==What is Pelargonidin?==
Pelargonidin and Cyanidin are both types of anthocyanidins. These are antioxidants that have been found to help improve blood vessel function in humans and animals.[http://www.5aday.com/html/phytochem/anthocyanidins.php 1] Anthocyanidins are found in blue, purple and red fruits and vegetables such as:
* blueberries
* blackberries
* plums
* cranberries
* raspberries
* strawberries.

Anthocyanidins have the general structure:

[[Image:Anthocyanidin.gif|thumb|anthocynaidin structure]]

The different R-groups determine the different types of anthocyanidin. Pelargonidin has a characteristic orange colour and Cyanidin has a characteristic orange-red colour.

Anthocyanidins are found in the cell's cell sap (unlike chlorophyll and carotene that are attatched to cell membranes). The colour of the pigment is altered by the pH of the cell sap. More acidic cell sap gives a red colour. Less acidic cell sap gives a more purple colour.<sup>2</sup>

==Commercial uses of the Pigments==
Anthocyanins are used in processed foods (drinks and confectionery) to avoid using synthetic additives. They are used as natural additives because they are brightly coluored and not subject to legal restrictions (as many synthetic additives are). They are also used for their nutraceutical (nutritionally beneficial) properties.

The problem with anthocyanins however, is that they can become instable during processing and storage.<sup>3</sup>

==References==
*1 - http://www.5aday.com/html/phytochem/anthocyanidins.php
*2 - http://scifun.chem.wisc.edu/chemweek/fallcolr/fallcolr.html
*3 - http://ift.confex.com/ift/2002/techprogram/paper_13499.htm

It:wilkinson

2006-11-14T14:07:38Z

Mjl105: /* Comparison with other catalysts: */ Adjustment of web link appearence

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and Stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>wilkinsoncat.mol

104112 0 0 0 1 V2000
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0
1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
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The formula for Wilkinsons Catalyst is C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh<sub>3</sub>)<sub>3</sub> is known to react with pyridine to lead to the 'reductive coupling of aldehydes'<sup>2</sup>. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh<sub>3</sub>)<sub>2</sub>]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==

This compound RhCl(PPh3) is a ''square planar'', 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of ''rhodium trichloride'' with ''triphenylphosphine''. The synthesis is conducted in refluxing ethanol.

RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> -> RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

In hydrogenation of an alken: Before activation, RhCl(PPh<sub>3</sub>)<sub>3</sub> is a ''square planar'' complex in which rhodium is in oxidation state 1. Then it loses one of the phenylphosine group. Dihydrogen, H<sub>2</sub>, is then homolytically dissociates into two hydrogen atoms which each coordinate to the rhodium oxidative addition: the metal's oxidation number increases to 3. The resulting ''octahedral'' complex then loses one of its phosphine ligands, which is replaced by the alkene.

One of the hydrogen atoms then transfers from the rhodium to the alkene, which becomes an alkyl ligand. The expelled phosphine ligand resumes its place in the complex and the remaining hydrogen then also transfers to the alkyl ligand, which becomes an alkane and leaves the complex. Thus the original Wilkinson complex, with all three phosphine ligands, is restored.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
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ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
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ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
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ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
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ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
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ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
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ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al<sub>2</sub>O<sub>3</sub> surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'<sup>1</sup>. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C<sub>54</sub>H<sub>45</sub>C<sub>l</sub>P<sub>3</sub>Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-11-14T13:57:16Z

Mjl105: /* An example of the Wilkinson Catalyst reaction: */ Adjustment of subscripts

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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104112 0 0 0 1 V2000
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0
1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
3.8158 -4.8684 -1.5308 C 0 0 0 0 0
3.6375 -3.8077 -0.6402 C 0 0 0 0 0
1.6930 -2.8219 1.9100 C 0 0 0 0 0
2.4316 -2.9296 3.0942 C 0 0 0 0 0
2.0614 -3.8291 4.0967 C 0 0 0 0 0
0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
2.1677 -1.6384 0.5153 P 0 3 0 0 0
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
-0.1140 4.8185 -5.4421 H 0 0 0 0 0
1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
4.3314 1.8231 -3.0516 H 0 0 0 0 0
6.1490 3.2015 -2.0911 H 0 0 0 0 0
6.0335 3.9578 0.2887 H 0 0 0 0 0
4.0574 3.3374 1.6885 H 0 0 0 0 0
2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
0.8200 -4.7186 -3.1578 H 0 0 0 0 0
2.9459 -6.0336 -3.1421 H 0 0 0 0 0
4.7305 -5.4811 -1.4819 H 0 0 0 0 0
4.4065 -3.6300 0.1274 H 0 0 0 0 0
3.3326 -2.3235 3.2645 H 0 0 0 0 0
2.6540 -3.8952 5.0239 H 0 0 0 0 0
0.6662 -5.3756 4.7074 H 0 0 0 0 0
-0.6272 -5.2652 2.5700 H 0 0 0 0 0
0.0300 -3.6842 0.7953 H 0 0 0 0 0
5.0569 -1.5000 -0.4374 H 0 0 0 0 0
7.0365 -0.3324 0.4516 H 0 0 0 0 0
6.8657 1.0364 2.5360 H 0 0 0 0 0
4.6632 1.2478 3.7011 H 0 0 0 0 0
2.6569 0.1188 2.7908 H 0 0 0 0 0
-3.1849 2.7955 -2.5425 H 0 0 0 0 0
-4.0593 2.2779 -4.7924 H 0 0 0 0 0
-3.4716 0.1205 -5.9078 H 0 0 0 0 0
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0
0.0849 2.3852 1.5776 H 0 0 0 0 0
0.8246 4.6387 2.2757 H 0 0 0 0 0
0.3629 6.6219 0.8221 H 0 0 0 0 0
-0.8555 6.3149 -1.3365 H 0 0 0 0 0
-1.5785 4.0746 -2.0551 H 0 0 0 0 0
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0
-5.2797 -1.3605 0.6443 H 0 0 0 0 0
-6.1750 0.3688 2.2115 H 0 0 0 0 0
-4.9429 2.5200 2.5189 H 0 0 0 0 0
-2.8474 2.9476 1.2892 H 0 0 0 0 0
1 20 1 6 0 0
1 39 1 0 0 0
1 40 1 1 0 0
1 41 1 0 0 0
2 3 2 0 0 0
2 7 1 0 0 0
2 20 1 1 0 0
3 4 1 6 0 0
3 60 1 0 0 0
4 5 2 0 0 0
4 61 1 6 0 0
5 6 1 1 0 0
5 62 1 6 0 0
6 7 2 0 0 0
6 63 1 0 0 0
7 64 1 1 0 0
8 9 2 0 0 0
8 13 1 1 0 0
8 20 1 0 0 0
9 10 1 0 0 0
9 65 1 6 0 0
10 11 2 0 0 0
10 66 1 6 0 0
11 12 1 1 0 0
11 67 1 0 0 0
12 13 2 0 0 0
12 68 1 1 0 0
13 69 1 1 0 0
14 15 2 0 0 0
14 19 1 0 0 0
14 20 1 1 0 0
15 16 1 6 0 0
15 70 1 0 0 0
16 17 2 0 0 0
16 71 1 6 0 0
17 18 1 1 0 0
17 72 1 6 0 0
18 19 2 0 0 0
18 73 1 0 0 0
19 74 1 1 0 0
21 22 2 0 0 0
21 26 1 0 0 0
21 39 1 1 0 0
22 23 1 6 0 0
22 75 1 0 0 0
23 24 2 0 0 0
23 76 1 6 0 0
24 25 1 1 0 0
24 77 1 6 0 0
25 26 2 0 0 0
25 78 1 0 0 0
26 79 1 1 0 0
27 28 2 0 0 0
27 32 1 0 0 0
27 39 1 6 0 0
28 29 1 1 0 0
28 80 1 0 0 0
29 30 2 0 0 0
29 81 1 1 0 0
30 31 1 6 0 0
30 82 1 1 0 0
31 32 2 0 0 0
31 83 1 0 0 0
32 84 1 6 0 0
33 34 2 0 0 0
33 38 1 1 0 0
33 39 1 0 0 0
34 35 1 0 0 0
34 85 1 6 0 0
35 36 2 0 0 0
35 86 1 6 0 0
36 37 1 1 0 0
36 87 1 0 0 0
37 38 2 0 0 0
37 88 1 1 0 0
38 89 1 1 0 0
41 42 1 6 0 0
41 48 1 0 0 0
41 54 1 1 0 0
42 43 2 0 0 0
42 47 1 0 0 0
43 44 1 6 0 0
43 90 1 1 0 0
44 45 2 0 0 0
44 91 1 0 0 0
45 46 1 1 0 0
45 92 1 6 0 0
46 47 2 0 0 0
46 93 1 0 0 0
47 94 1 1 0 0
48 49 2 0 0 0
48 53 1 6 0 0
49 50 1 0 0 0
49 95 1 1 0 0
50 51 2 0 0 0
50 96 1 1 0 0
51 52 1 6 0 0
51 97 1 0 0 0
52 53 2 0 0 0
52 98 1 6 0 0
53 99 1 6 0 0
54 55 2 0 0 0
54 59 1 1 0 0
55 56 1 1 0 0
55100 1 6 0 0
56 57 2 0 0 0
56101 1 0 0 0
57 58 1 0 0 0
57102 1 1 0 0
58 59 2 0 0 0
58103 1 1 0 0
59104 1 0 0 0
M END</inlineContents>
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The formula for Wilkinsons Catalyst is C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh<sub>3</sub>)<sub>3</sub> is known to react with pyridine to lead to the 'reductive coupling of aldehydes'<sup>2</sup>. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh<sub>3</sub>)<sub>2</sub>]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==

This compound RhCl(PPh3) is a ''square planar'', 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of ''rhodium trichloride'' with ''triphenylphosphine''. The synthesis is conducted in refluxing ethanol.

RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> -> RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

In hydrogenation of an alken: Before activation, RhCl(PPh<sub>3</sub>)<sub>3</sub> is a ''square planar'' complex in which rhodium is in oxidation state 1. Then it loses one of the phenylphosine group. Dihydrogen, H<sub>2</sub>, is then homolytically dissociates into two hydrogen atoms which each coordinate to the rhodium oxidative addition: the metal's oxidation number increases to 3. The resulting ''octahedral'' complex then loses one of its phosphine ligands, which is replaced by the alkene.

One of the hydrogen atoms then transfers from the rhodium to the alkene, which becomes an alkyl ligand. The expelled phosphine ligand resumes its place in the complex and the remaining hydrogen then also transfers to the alkyl ligand, which becomes an alkane and leaves the complex. Thus the original Wilkinson complex, with all three phosphine ligands, is restored.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

<jmol>
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<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
END</inlineContents>
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al<sub>2</sub>O<sub>3</sub> surface to catalyse the hydrogenation reaction of olefins.

Ref:
Journal of Molecular Catalysis A: Chemical
Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152
or http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C<sub>54</sub>H<sub>45</sub>C<sub>l</sub>P<sub>3</sub>Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-11-14T13:55:57Z

Mjl105: /* Structure and Synthesis */ Adjustment to picture note

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
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3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
3.8158 -4.8684 -1.5308 C 0 0 0 0 0
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2.4316 -2.9296 3.0942 C 0 0 0 0 0
2.0614 -3.8291 4.0967 C 0 0 0 0 0
0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
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-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
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-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
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1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
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6.1490 3.2015 -2.0911 H 0 0 0 0 0
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2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
0.8200 -4.7186 -3.1578 H 0 0 0 0 0
2.9459 -6.0336 -3.1421 H 0 0 0 0 0
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3.3326 -2.3235 3.2645 H 0 0 0 0 0
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0.6662 -5.3756 4.7074 H 0 0 0 0 0
-0.6272 -5.2652 2.5700 H 0 0 0 0 0
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The formula for Wilkinsons Catalyst is C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh<sub>3</sub>)<sub>3</sub> is known to react with pyridine to lead to the 'reductive coupling of aldehydes'<sup>2</sup>. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==

This compound RhCl(PPh3) is a ''square planar'', 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of ''rhodium trichloride'' with ''triphenylphosphine''. The synthesis is conducted in refluxing ethanol.

RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> -> RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

In hydrogenation of an alken: Before activation, RhCl(PPh<sub>3</sub>)<sub>3</sub> is a ''square planar'' complex in which rhodium is in oxidation state 1. Then it loses one of the phenylphosine group. Dihydrogen, H<sub>2</sub>, is then homolytically dissociates into two hydrogen atoms which each coordinate to the rhodium oxidative addition: the metal's oxidation number increases to 3. The resulting ''octahedral'' complex then loses one of its phosphine ligands, which is replaced by the alkene.

One of the hydrogen atoms then transfers from the rhodium to the alkene, which becomes an alkyl ligand. The expelled phosphine ligand resumes its place in the complex and the remaining hydrogen then also transfers to the alkyl ligand, which becomes an alkane and leaves the complex. Thus the original Wilkinson complex, with all three phosphine ligands, is restored.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
END</inlineContents>
</jmolApplet>
</jmol>

The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al<sub>2</sub>O<sub>3</sub> surface to catalyse the hydrogenation reaction of olefins.

Ref:
Journal of Molecular Catalysis A: Chemical
Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152
or http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C<sub>54</sub>H<sub>45</sub>C<sub>l</sub>P<sub>3</sub>Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:Vanillin

2006-11-14T10:36:03Z

Mjl105: /* Vanillin */ Addition of 3D Eugenol Jmol

It:Vanillin

2006-11-14T10:28:37Z

Mjl105: /* Vanillin */ Addition of 3D Jmol of Vanillin

It:Vanillin

2006-11-14T10:19:43Z

Mjl105: Addition of first details

== Vanillin ==

Natural vanillin is the main component of oil of vanilla, the essential oil (the fragrance of a plant) obtained from a type of orchid called ''Vanilla fragrans'' or vanilla orchid. Most essential oils are obtained by distilling the leaves or petals of the plant over steam but oil of vanilla is extracted from the dried, fermented seed pods.

Most essentials oils are usually used in the perfume industry although some are also used in the food industry, particularly to flavour foods. Vanillin is used widely in both and because of this there is not enough natural supply to meet demand and so therefore has to be synthesised. This is mainly done by the oxidation of eugenol (which can be found in oil of bay found in bay leaves).